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I am with dmc on this. I needed to reach a threshold of capital and investment income before I felt the track was clear.

Looking back on the years since early retirement, I was basically accurate on most of my assumptions. A major exception was the rate of increase in the cost of private individual health insurance. I expected increases, but not at double-digit rates year after year. I had high deductible coverage from age 50 to 62... never had a claim that exceeded the deductible... so basically I "coulda" bought a new Bentley Continental Coupe GT with the money I paid for health insurance over those years. Sigh. I was probably better off being insured for catastrophic medical expenses than I would be on the open road driving a purring Bentley.

I like to think the insurance company bought the Bentley with my premiums. <wink>

Sometimes I think of the money I could have made, but still not missing the work, and time at work. I’ve been retired now for 10 years and still have 5 years to go till 65. Been paying 15-20k a year for health insurance also, and that’s with after tax money. And that would be worth much more with the gains we’ve had in the stock market over that time frame.

And the 250k a year in income, before taxes, would still add up to a tidy sum if you also factor in the market gains.

But the last 10 years have been great and there is no promise of tommorow. My mom passed away at 55, and the owner of the company that I worked at, also a good friend died at 57. Also I’m still pretty healthy, but I know I’ll never be as good at golf as I was 25-30 ago. And my hearing and vision is definatly not as good. And I’m pretty sure the outlook as I get older is not promising. So I’m glad I’ve had the last 10 years to do pretty much what I wanted with my time.

When im in town I’ll stop in where I use to work and have lunch and visit. And I still go to the Christmas party from time to time. But I don’t miss the work, and I visit less now.

My wife is a cancer survivor, so we are not putting things off for tommorow if we can do them today. I know several who died just before retiring or just after. It wasn’t being retired that did them in, it was they waited to long to quit. It was always just one more year. I was at the funeral of a Vice President of the company I worked for. One of the speakers said he was working on some projects a few days before he died while he was at the hospital. They thought his dedication was a good thing, I thought it was sad.

We could have retird at 55 and been fine. But—worry about money would have been there for me. I dont know how to put a price on “the worry” but I think it would have been in the ball park of stress at work, dont know. Still, I wish I had retired at 59 instead of 60 so that I could say “I retired in my 50’s.”